866 Pendleton Point Road, Islesboro, ME 04848

$5,750,000
Property Type: Residential Bedrooms: 6 Baths: 9 Square Footage: 9,449 Lot Size (sq. ft.): 228,690 Status: Active
Current Price: $5,750,000 List Date: 6/16/2026 Last Modified: 7/17/2026

Overview

Description

East Bay is an exceptional coastal estate offering the perfect blend of a private summer retreat and a tranquil year-round residence. Set on more than five secluded acres with 430 feet of pristine, accessible waterfront, the property enjoys an elevated position above the scenic shoreline, where beautifully curated gardens and mature landscaping frame sweeping views across Penobscot Bay and its islands. The residence unfolds along a gently sloping bluff, capturing spectacular water vistas from nearly every room and outdoor living space. Originally built as a post-and-beam home around 2000, East Bay has been thoughtfully transformed over time. Its current design, inspired by the timeless coastal architecture of Royal Barry Wills, combines classic New England character with understated sophistication. Designed for both elegant entertaining and comfortable everyday living, the home offers a seamless balance of formal and informal spaces. Highlights include a first-floor primary suite ...

Listing Details MLS# 1667521

Property Sub-Type

Property Sub-Type
Single Family Residence

Location Information

Street #
866
Street Name
Pendleton Point
Street Type
Road
County
Waldo
Town
Islesboro
State/Province
ME
Zip Code
04848
Zip +4
5159
Leased Land
No
Book
4820
Page
172
Map
6
Lot
6
Zoning
Shoreland Res
Zoning Overlay
Unknown
Association
No
Full Tax Amount $
47732
Tax Year
2025
Tree Growth Y/N
No

Contract Information

Original List Price
5750000

Property Information

Surveyed
Unknown
Seasonal
No
# Rooms
19
# Bedrooms
6
# Fireplaces
4
Total Full Baths
6
Total Half Baths
3
Total Baths
9
Year Built
2000
SqFt Finished Above Grade
8696
SqFt Finished Below Grade
753
SqFt Finished Total
9449
SqFt Source
Other
Other Source of Square Footage
Matterport Floor Plans, Estimated
Garage
No
Lot Size Acres +/-
5.25
Source of Acreage
Public Records
Road Frontage
No

Water Info

Waterfront
Yes
Waterfront Amount
429
Water Frontage Owned
429
Water View
Yes
Water Body Name
Penobscot Bay, Ocean

Appliances Included

Other Appliances
See listing remarks

More Information

Vehicle Storage

Attached
Yes

Bedroom 2

Bedroom 2
Yes
Bedroom 2 Level
Second

Bedroom Amenities 2

Closet
Yes
Full Bath
Yes

Bedroom 3

Bedroom 3
Yes
Bedroom 3 Level
Second

Bedroom Amenities 3

Closet
Yes
Full Bath
Yes

Bedroom 4

Bedroom 4
Yes
Bedroom 4 Level
Second

Bedroom Amenities 4

Closet
Yes
Full Bath
Yes

Bedroom 5

Bedroom 5
Yes
Bedroom 5 Level
Second

Bedroom Amenities 5

Closet
Yes
Full Bath
Yes

Bedroom 6

Bedroom 6
Yes
Bedroom 6 Level
Second

Bedroom Amenities 6

Closet
Yes
Full Bath
Yes

Dining Room

Dining Room
Yes
Dining Room Level
First

Dining Room Amenities

Wood Burning Fireplace
Yes

Exercise Room

Exercise Room
Yes
Exercise Room Level
Basement

Great Room

Great Room
Yes
Great Room Level
Second

Great Room Amenities

Vaulted Ceiling
Yes
Wood Burning Fireplace
Yes

Kitchen

Kitchen
Yes
Kitchen Level
First

Kitchen Amenities

Eat-in Kitchen
Yes

Laundry Room

Laundry
Yes
Laundry Room Level
First

Library

Library
Yes
Library Level
First

Library Amenities

Wood Burning Fireplace
Yes

Living Room

Living Room
Yes
Living Room Level
First

Living Room Amenities

Built-Ins
Yes
Vaulted Ceiling
Yes
Wood Burning Fireplace
Yes

Primary Bedroom

Primary Bedroom
Yes
Primary Bedroom Level
First

Primary Bedroom Amenities

Closet
Yes
Double Vanities
Yes
Full Bath
Yes
Separate Shower
Yes
Soaking Tub
Yes
Suite
Yes
Sunken/Raised
Yes
Walk-in Closet
Yes

Office

Office
Yes
Office Level
First

Office Amenities

Heat Stove Hookup
Yes

Other Room 1

Other Room 1
Yes
Other Room 1 Level
First

Other Room 2

Other Room 2
Yes
Other Room 2 Level
Basement

Other Room 3

Other Room 3
Yes
Other Room 3 Level
Basement

Room Features

Built-Ins
Yes
Closet
Yes
Double Vanity
Yes
Eat-in Kitchen
Yes
Full Bath
Yes
Heat Stove Hookup
Yes
Separate Shower
Yes
Soaking Tub
Yes
Suite
Yes
Sunken/Raised
Yes
Vaulted Ceiling(s)
Yes
Walk-In Closet(s)
Yes
Wood Burning Fireplace
Yes

Property Features

Site: Level; Open; Other Site; Rolling/Sloping; Well Landscaped Location: Near Country Club; Near Golf Course; Near Public Beach; Other Location Roads: Public Source of Water Frontage: Public Records Water Body Type: Bay; Ocean View: Scenic Appliances Included: Dishwasher; Dryer; Electric Range; Gas Range; Microwave; Refrigerator; Wall Oven; Washer; Other Style: Shingle Construction: Wood Frame Basement: Crawl Space; Finished; Full; Partial; Unfinished Basement Entry: Bulkhead; Interior Foundation Materials: Poured Concrete Roof: Shingle Exterior: Wood Siding Heat System: Forced Air; Heat Pump; Hot Water; Zoned Heat Fuel: Oil; Propane Water Heater: Off Heating System Cooling: Heat Pump Floors: Carpet; Tile; Wood Amenities: 1st Floor Primary Bedroom w/Bath; Bathtub; Irrigation System; Laundry - 1st Floor; Laundry - 2nd Floor; Other; Pool-In Ground; Primary Bedroom w/Bath; Shower; Storage; Walk-in Closets Equipment: Generator; Internet Access Available Driveway: Gravel Parking: 5 - 10 Spaces Vehicle Storage: 1 Car; Carport Electric: Circuit Breakers Gas: Bottled Sewer: Private Sewer Water: Private; Well

Room Information

Room Name Level
Primary Bedroom First
Bedroom 2 Second
Bedroom 3 Second
Bedroom 4 Second
Bedroom 5 Second
Bedroom 6 Second
Other Room First
Library First
Living Room First
Dining Room First
Kitchen First
Office First
Great Room Second
Office Second
Laundry First
Office First
Exercise Room Basement
Other Room 3 Basement
Other Room 2 Basement

Documents

IDX
Listing Office: Legacy Properties Sotheby's International Realty
Last Updated: July - 17 - 2026
Listing data is derived in whole or in part from the Maine IDX and is for consumers' personal, noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. Copyright ©2026 Maine Real Estate Information System, Inc. All Rights Reserved. Equal Housing Opportunity.